Customer Success AI Operations Lead

Bitsight is a cyber risk management leader transforming how companies manage exposure, performance, and risk for themselves and their third parties. Companies rely on Bitsight to prioritize their cybersecurity investments, build greater trust within their ecosystem, and reduce their chances of financial loss.
Built on over a decade of technological innovation, its integrated solutions deliver value across enterprise security performance, digital supply chains, cyber insurance, and data analysis.

• We invented the cyber ratings industry in 2011
• Over 3000 customers trust Bitsight
• Over 750 teammates are dispersed throughout Boston, Raleigh, New York, Lisbon, Singapore, and remote

We are building an AI-native Customer Success operating model from the ground up, and we’re looking for a hands-on builder/operator to help bring it to life.

This role sits at the intersection of Customer Success, operations, AI, data, systems, and workflow design. The ideal candidate can take a clear business vision, rapidly prototype solutions, gather feedback, iterate quickly, and turn early ideas into scalable workflows that help the CS team operate with more speed, intelligence, and consistency.

This is not a traditional CS Ops administration role or a pure strategy role. This person will be expected to build. You’ll work closely with CS leadership to design and implement AI-enabled workflows across lifecycle management, customer health, risk detection, renewal readiness, executive engagement, EBR/QBR preparation, digital engagement, support deflection, and CSM productivity.

The right person is technically curious, highly resourceful, comfortable with ambiguity, and genuinely excited by the opportunity to use AI to redesign how Customer Success work gets done.

What You’ll Do

• Build AI-powered workflows, automations, prompts, templates, and tools that reduce manual work and improve CS execution.

• Prototype and scale workflows such as automated EBR/QBR decks, renewal briefs, customer summaries, risk narratives, meeting prep, and next-best-action recommendations.

• Help operationalize the CS operating model, including lifecycle stages, health and risk models, renewal readiness, executive engagement, customer prioritization, and value tracking.

• Partner with CS, RevOps, Data, Support, Product, and other teams to connect the right data into the right workflows.

• Work across systems such as Salesforce, Gainsight, Clari, Gong, Zendesk, Snowflake, Slack, Zoom, Google Workspace, Claude, ChatGPT, and other AI/automation tools.

• Establish prompt structures, QA checks, feedback loops, and documentation to ensure AI outputs are useful, accurate, and scalable.

• Gather feedback from CSMs and leaders, iterate quickly, and continuously improve workflows based on real team usage.

• Help CSMs spend less time on manual reporting, prep, and coordination, and more time on high-value customer engagement.

What Success Looks Like

In the first 90 days, you will:

• Learn the CS operating model, current workflows, core systems, and biggest pain points.

• Identify the highest-impact opportunities for AI and automation across the CS lifecycle.

• Ship several practical AI-enabled workflows that reduce manual CSM effort.

• Build repeatable prompt, QA, and feedback processes.

• Help operationalize core lifecycle, health, risk, renewal, or EBR/QBR workflows.

• Demonstrate measurable impact on CSM productivity, consistency, or customer-facing output quality.

Over time, you will help build a scalable AI and automation layer across the customer lifecycle and establish CS Ops as a strategic engine for scale, efficiency, and customer impact.

What We’re Looking For

• 2–6+ years of experience in Customer Success Operations, Revenue Operations, Support Operations, Technical Account Management, Solutions Consulting, Customer Success, Technical Support, or a similar role.

• Demonstrated experience using AI tools to build practical workflows, automations, internal tools, summaries, agents, or business processes.

• Strong builder/operator mindset with a bias toward fast prototyping and iteration.

• Comfort working with CRM, CS, support, revenue, or data systems.

• Ability to take loosely defined ideas and turn them into structured execution.

• Strong systems thinking across process, data, tools, and user experience.

• Comfortable operating in ambiguity and making pragmatic tradeoffs.

• Strong cross-functional communication and documentation skills.

• High ownership, attention to detail, and willingness to incorporate feedback quickly.

Preferred Experience

• Hands-on experience with Salesforce, Gainsight, Gong, Clari, Zendesk, Slack, Zoom, Google Workspace, or similar GTM tools.

• Experience with Claude, Claude Code, ChatGPT, Gemini, Cursor, Replit, or other modern AI tools.

• Experience with automation tools such as Zapier, Make, Workato, n8n, Tray.io, or similar platforms.

• Familiarity with Snowflake, SQL, data warehouses, BI tools, or data modeling concepts.

• Experience building workflows that use CRM, call, support, product, or customer data.

• Customer-facing experience in CS, Support, TAM, Solutions Consulting, or Technical Support.

• Basic scripting, API, or low-code/no-code automation experience.

• Experience administering or configuring GTM systems.

Belonging & Inclusion. Bitsight is proud to be an equal opportunity employer. This means we do not tolerate discrimination of any kind and are committed to providing equal employment opportunities regardless of your gender identity, race, nationality, religion, sexual orientation, status as a protected veteran, or status as an individual with a disability.

Culture. We put our people first. Bitsight offers best in class benefits. We devote the same energy to nurturing our company's inclusive culture as we apply to serving our customers' needs. Working at Bitsight will give you the opportunity to fulfill your professional goals and expand your skills.

Open-minded. If you got to this point, we hope you’re feeling excited about the job description you just read.  Even if you don’t feel that you meet every single requirement, we still encourage you to apply.  We’re eager to meet people that believe in Bitsight’s mission and can contribute to our team in a variety of ways.

Bitsight also provides reasonable accommodations to qualified individuals with disabilities or based on a sincerely held religious belief in accordance with applicable laws. If you need to inquire about a reasonable accommodation, or need assistance with completing the application process, please email recruiting@bitsight.com. This contact information is for accommodation requests only, and cannot be used to inquire about the status of applications.

Additional Information for United States of America Applicants:

Bitsight is committed to compliance with all fair employment practices regarding citizenship and immigration status.

Bitsight will not discharge, discipline or in any other manner discriminate against any employee or applicant for employment because such employee or applicant has inquired about, discussed, or disclosed the compensation of the employee or applicant or another employee or applicant.

Massachusetts Applicants: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Qualified applicants with criminal histories will be considered for employment consistent with applicable law.

This position may be considered a promotional opportunity pursuant to the Colorado Equal Pay for Equal Work Act.

The anticipated hiring base salary range for this position is US$78,980 to $117,000 annually for US-based employees.  This range reflects the minimum and maximum target for new hire salaries for the position across all US locations, is based on a full-time work schedule, and is Bitsight’s good faith estimate as of the date of this posting.  Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training.

In addition to base salary, this role is eligible for participation in a bonus or commission plan and an equity grant.  Bitsight also offers a competitive benefits package, including but not but limited to medical, dental, and vision insurance; paid parental leave; flexible time off; a 401(k) plan with employee and company contribution opportunities; life and disability insurance; and tuition reimbursement.